mesosulfuron-methyl
Herbicide
HRAC B WSSA 2; sulfonylurea
NOMENCLATURE
Common name mesosulfuron-methyl (BSI, pa ISO)
IUPAC name methyl 2-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-a-(methanesulfonamido)-p-toluate
Chemical Abstracts name methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-4-[[(methylsulfonyl)amino]methyl]benzoate
CAS RN [208465-21-8] Development codes AE F130060; AE F154851 (acid) (both AgrEvo)
PHYSICAL CHEMISTRY
Mol. wt. 503.5 M.f. C17H21N5O9S2 Form Cream-coloured solid. M.p. 195.4 °C V.p. 1.1 ´ 10-8 mPa (25 °C) KOW logP = 1.39 (pH 5), -0.48 (pH 7), -2.06 (pH 9). Henry 2.434 ´ 10-10 Pa m3 mol-1 (pH 5, 20 °C) Solubility In water 7.24 ´ 10-3 (pH 5), 0.483 (pH 7), 15.39 (pH 9) (all in g/l, 20 °C). Stability Stable to photolysis. Abiotic hydrolysis DT50 3.5 (pH 4), 253 (pH 7), 319 (pH 9) (all in d, 25 °C).
COMMERCIALISATION
History Reported by E Hacker et al., (Proc. BCPC Conf. - Weeds, 2001, 1, 43), discovered in 1996, and under development by Aventis CropScience (now Bayer CropScience). Manufacturers Bayer CropScience
APPLICATIONS
Biochemistry Branched chain amino acid synthesis (ALS or AHAS) inhibitor. Acts by inhibiting biosynthesis of the essential amino acids valine and isoleucine, hence stopping cell division and plant growth. Mefenpyr-diethyl enhances metabolism of the herbicide selectively in cereal crop plants. Uses For early to mid post-emergence control of grass and some broad-leaved weeds in winter, spring and durum wheat, triticale and rye, at 15 g/ha. For use in combination with mefenpyr-diethyl at 45 g/ha. Selected products: mixtures: 'Mesomaxx' (+ mefenpyr-diethyl) (Bayer CropScience)
OTHER PRODUCTS
Mixtures: 'Archipel' (+ iodosulfuron-methyl-sodium+ mefenpyr-diethyl) (Bayer CropScience); 'Atlantis' (+ iodosulfuron-methyl-sodium+ mefenpyr-diethyl) (Bayer CropScience); 'Cossack' (+ iodosulfuron-methyl-sodium+ mefenpyr-diethyl) (Bayer CropScience)
MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute dermal LD50 for rats >5000 mg/kg. Non-irritating to skin slightly irritant to eyes (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 >1.33 mg/l air. Other Not mutagenic.
ECOTOXICOLOGY
Birds Not toxic. Fish LC50 (96 h) 100 mg/l. Algae LC50 (96 h) 0.21 mg/l. Other aquatic spp. EC50 (7 d) for Lemna gibba 0.6mg/l. Bees Not toxic. Worms Not toxic.
ENVIRONMENTAL FATE
Soil/Environment Readily degraded, probably mainly by a microbial processes. Soil DT50 8-68 d (mean 39.1 d). Mesosulfuron-methyl and its metabolites are not transported in soil below 1 m, at or above the EU threshold for drinking water.
|